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Cocked to the right or left, angled off-kilter, covering one ear or another — all different attitudes, depending on the day, depending on how he’s feeling.

Hats, said Jessen Fitzpatrick of Jamaica Plain’s headwear boutique Salmagundi, are a signature — drawing out a personality, emphasizing a mood, revealing “a part of you that you didn’t notice before.’’

Fashionable head-toppers aren’t the everyday accoutrement they once were — maybe, as it’s been theorized, their decline was influenced by “Hatless Jack’’ John F. Kennedy. Maybe it was the proliferation of the automobile. Maybe the ease and functionality of the baseball cap in the latter decades of the 20th century simply eclipsed dressier options.

And yet, for youthful, stylish types, hats are again a wardrobe staple. It is no passing fad. Pop culture icons are now rarely photographed bareheaded: Tom Brady sports his newsboy cap, Justin Timberlake has his porkpie, Snoop Dog, his beanie. Britney, Rihanna, Katy Perry — they all have a cache.

And so it is for (many) of the rest of us. Fitzpatrick and his wife, Andria Rapagnola, make a living selling hats at Salmagundi, where measuring tapes are always unfurled for their menagerie of habitual, and sometimes slightly obsessive, hat-wearers.

In fact, the colorful, whimsical rectangle snug among the collection of shops on Centre Street underwent an expansion this fall that nearly doubled its inventory and boosted its offerings of custom and exclusive headgear.

“People are being more experimental with fashion,’’ said Fitzpatrick. Although fedoras, cloches, flat caps, and trilbies will never cover every cranium, he admitted, Salmagundi’s crowning wares are “definitely more accepted’’ these days.

And they’re mandatory among the clientele.

“I don’t think you can have enough hats,’’ said John Kramer, a composer and pianist from Jamaica Plain, who won’t go out without one. Considering it an essential wardrobe piece, he and his wife own roughly 30 combined, both dressy and casual. “They’re a fun accessory for life.’’

But this isn’t the stuff of Dr. Seuss or “Alice in Wonderland.’’ When Fitzpatrick and Rapagnola (just try and catch them with their heads uncovered) first tipped their brims into the business, they saw the industry vacillating between the ultra-classic Frank Sinatra and the flamboyant Flavor Flav. They wanted their wares to represent various eras, but also be “teetering the line of edginess,’’ Fitzpatrick explained from his perch on a stool in a narrow, stuffed storage room beneath Salmagundi. It is so crowded that, in some places, one must inhale deeply and contort to navigate the space. “We combine those two worlds.’’

Upstairs, just beyond the hustle of Centre Street, there are hats as far as the eye can see.

On walls or floor stands are traditional outback hats, crowns tucked one into the other. There are top hats with floral blooms, cascading fedoras flared with peacock feathers or striped bands, one of them in lollipop red.

Berets and five point ivys are stacked on tables and garden chairs like Sunday-morning pancakes. Cloches — the snug, bell-shaped caps favored by the flappers of the 1920s — flourish in a chromatic spectrum of ultraviolet purples, yellows, burgundies, leopard prints, or pinstripes, some embellished with zippers, ribbons, and flowers.

“They get it, they understand that there’s this whole other group of people that were not being serviced,’’ said milliner Dina Pisani — of the Brooklyn-based Cha Cha’s House of Ill Repute — who creates custom Salmagundi designs. “Younger clients don’t just want the standard old-man’s hat.’’

To meet that demand, Salmagundi maintains a cache of roughly 6,000 headpieces — several dozen of which are exclusive designs — representing both international brands and independent designers like Pisani, whose handmade hats include vintage baubles or other unique, one-of-a-kind flairs.

It’s a motley assortment — and pursuit — reflected in Salmagundi’s very name, derived from the French word “salmigondis,’’ meaning a disparate assembly of things, ideas, or people forming an incoherent whole.

Which is also an analogue for their customers.

Being one of only a half-dozen hat stores in New England, Salmagundi has become a destination, with devoted hat-wearers traveling from all over the region and New York, Rapagnola noted.

“It’s millionaires to blue collar, and they’ll hang out together,’’ said Fitzpatrick, who creates an ambiance with seasonal playlists that include jazz, Latin, soul, funk, and classics. “We cater to a diverse crowd, culturally and economically.’’

It all started in a vaudeville-like fashion. For about six months, Fitzpatrick and Rapagnola — both 34 and parents to 9-month-old Theo — worked as traveling vendors, setting up a boutique at music festivals and other events, eventually developing a sort of cultish following. (And yes, they get the “mad hatter’’ thing all the time. Fitzpatrick’s response? “I’m a happy hatter.’’)

They’d both long been budding fashionistas: Rapagnola, with a degree in fine arts, recalls high school days fighting bad prints and jeans rolled-up into multicolored socks; Fitzpatrick, in turn, battled business casual while in corporate finance.

“Everyone had the blue shirt and the khakis,’’ he said. “I’d find ways to work the dress code.’’ Now, the stylish couple, whose words weave into one another’s with expressions like “jazzy’’ and “rock it,’’ can’t imagine roaming through life with heads bare.

She prefers flat caps, he likes fedoras. They each pick four to six per season, and often get “stuck in one,’’ said Fitzpatrick. (For the moment, he’s committed to a gray wool fedora with a 2-inch brim, a signature his hairdresser gladly snips around.)

But obviously, not everyone can wear a hat, right?

Rapagnola gives a skeptical squint and breaks out the air quotes. “People say they’re not a ‘hat person.’ What does that mean? It’s like saying, ‘I’m not a shoe person.’ ’’

“There’s a hat for everybody,’’ Fitzpatrick agreed. “You just have to find the right one.’’

In hats, they see many metaphors. Getting your first can be a “gateway drug,’’ the beginning of a full-blown addiction. Fitzpatrick also compared the hat-search process to dating: You can’t just settle for the first one you try on.

“Sometimes the first one’s good, though,’’ Rapagnola reminded him.

Still, it’s not about merely putting a hat on. As Sinatra once put it: “Cock your hat, angles are attitudes.’’

“There’s no wrong way,’’ said Rapagnola, her felted brown fedora with its 1 1/2-inch brim tilted to the right, half covering her right ear and flattening her brunette ponytail.

FEDORA: A mainstay. Most often associated with Frank Sinatra, Humphrey Bogart, or Indiana Jones, this classic style is known for its brim and creased crown and is now acceptably unisex. “The last time it was inappropriate for women to wear a fedora, it was also inappropriate for them to wear pants,’’ explained Jessen Fitzpatrick. Felts, colors, trims, brim widths, and crown shapes and lengths shift by season.

BERET: No longer a cliche or worn only by beatniks or the French. Brimless, flat, and round, they come in a variety of felts, wools, knits, faux furs, and leather for both men and women. Some are festooned with buttons, flowers, and studs. Occasionally oversize.

CLOCHE: Imagine a 1920s “flapper’’ girl, and you’ve got it. A cloche is a bell-shape hat that snugly cups the head. Available in a prism of colors, and also printed, flowered, studded, pinstriped, buttoned, or demurely bowed.

FLAT CAP: You might remember your grandfather wearing one — or your taxi driver. The flat cap sports a rounded back and a stiff, protruding front brim. Most abundant in a diversity of tweeds and plaids.

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